Description

2-(Iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 70557-99-2) is a highly specialized organoboron compound with the molecular formula C₇H₁₄BIO₂. This reagent is widely utilized in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, due to its stability and reactivity as a boronic ester. The compound features a dioxaborolane backbone with an iodomethyl substituent, making it a versatile intermediate for constructing complex molecular architectures. It is supplied as a crystalline solid with high purity (>95%) and is stored under inert conditions to ensure stability. Ideal for researchers in pharmaceuticals, agrochemicals, and materials science, this product is rigorously tested for quality and consistency.

Properties

• CAS Number: 70557-99-2
• Complexity: 143
• IUPAC Name: 2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C7H14BIO2/c1-6(2)7(3,4)11-8(5-9)10-6/h5H2,1-4H3
• InChI Key: UBNNPAYFVZFWPE-UHFFFAOYSA-N
• Exact Mass: 268.01316
• Molecular Formula: C7H14BIO2
• Molecular Weight: 267.90
• SMILES: B1(OC(C(O1)(C)C)(C)C)CI
• Topological: 18.5
• Monoisotopic Mass: 268.01316
• Synonyms: 70557-99-2, 2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, DTXSID00447779, DTXCID90398600, 818-567-5, Iodomethylboronic acid, pinacol ester, Iodomethylboronic acid pinacol ester, 2-Iodomethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, MFCD12405515, 1,3,2-Dioxaborolane, 2-(iodomethyl)-4,4,5,5-tetramethyl-, UBNNPAYFVZFWPE-UHFFFAOYSA-N, Iodomethylboronic acid,pinacol ester, Pinacol iodomethaneboronate, C7H14BIO2, SCHEMBL3197440, AKOS024262367, CS-W005567, GS-6151, FI160640, SY031094, (IODOMETHYL)BORONIC ACID PINACOL ESTER, EN300-244109, F11623, Z1269164084, 2-(Iodomethyl)-4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolane

Application

2-(Iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a key reagent in palladium-catalyzed cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex organic molecules. It is particularly useful in medicinal chemistry for the synthesis of boron-containing drug candidates. The compound’s stability under mild conditions makes it suitable for multi-step synthetic routes. Researchers also employ it in the development of advanced materials, such as organic semiconductors and polymers.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (66.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H319 (33.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Dam. 1 (66.7%)
• Eye Irrit. 2 (33.3%)
• STOT SE 3 (66.7%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.